An alternative fate of taraxasteryl cation in young shoots of Rosa multiflora: Deprotonation of H-19 produces taraxast-19-en-3β-ol and related triterpenoids

IF 1.3 4区生物学 Q4 CHEMISTRY, MEDICINAL

Phytochemistry Letters Pub Date : 2024-08-21 DOI:10.1016/j.phytol.2024.08.006

Marika Furuya, Taichi Akano, Hiroshi Araya, Yoshinori Fujimoto

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引用次数: 0

Abstract

Taraxast-19-en-3β-ol (1) and taraxast-19-en-3-one (2) were isolated from the surface lipids of young shoots of Rosa multiflora Thunb. The results provide the first evidence that deprotonation of H-19 can occur to produce the tetra-substituted triterpenes, in addition to the known formation taraxasterol and ϕ-taraxasterol by deprotonation of H-30 and H-21, respectively. Furthermore, taraxast-19(29)-ene-3β,20α-diol (3), which is presumed to be formed from compound 1 was isolated. The structures of the new compounds 1-3 with the α-orientation of H-18 were determined by spectroscopic methods including NOE studies. In addition, 19,20-seco-3β-hydroxyursane-19,20-dione (4), a 3β-hydroxy analog of the known 19,20-seco-ursane-3,19,20-trione was isolated. It is of note that compound 4 has the β-orientation of H-18, which is opposite to the α-orientation of H-18 of compounds 1-3.

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多花蔷薇幼芽中 taraxasteryl 阳离子的另一种命运：H-19的去质子化作用产生蒲公英甾-19-烯-3β-醇和相关三萜类化合物

研究人员从多花蔷薇（Rosa multiflora Thunb.）幼芽的表面脂质中分离出了蒲公英甾-19-烯-3β-醇（1）和蒲公英甾-19-烯-3-酮（2）。研究结果首次证明，除了已知的通过 H-30 和 H-21 的去质子化作用分别生成的 taraxasterol 和 ϕ-taraxasterol 外，H-19 也可发生去质子化作用生成四取代的三萜类化合物。此外，还分离出了塔拉司特-19(29)-烯-3β,20α-二醇（3），据推测它是由化合物 1 生成的。通过光谱方法（包括 NOE 研究）确定了 H-18 为 α 取向的新化合物 1-3 的结构。此外，还分离出了 19,20-seco-3β-羟基乌苏烷-19,20-二酮（4），它是已知的 19,20-seco-乌苏烷-3,19,20-三酮的 3β- 羟基类似物。值得注意的是，化合物 4 的 H-18 具有 β 取向，与化合物 1-3 的 H-18 的 α 取向相反。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Phytochemistry Letters 生物-生化与分子生物学

CiteScore

3.00

自引率

11.80%

发文量

190

审稿时长

34 days

期刊介绍： Phytochemistry Letters invites rapid communications on all aspects of natural product research including: • Structural elucidation of natural products • Analytical evaluation of herbal medicines • Clinical efficacy, safety and pharmacovigilance of herbal medicines • Natural product biosynthesis • Natural product synthesis and chemical modification • Natural product metabolism • Chemical ecology • Biotechnology • Bioassay-guided isolation • Pharmacognosy • Pharmacology of natural products • Metabolomics • Ethnobotany and traditional usage • Genetics of natural products Manuscripts that detail the isolation of just one new compound are not substantial enough to be sent out of review and are out of scope. Furthermore, where pharmacology has been performed on one new compound to increase the amount of novel data, the pharmacology must be substantial and/or related to the medicinal use of the producing organism.